228412-76-8

Basic information

• Product Name: 3-nitro-1-(p-toluenesulfonyl)indole
• Synonyms: 3-nitro-1-(p-toluenesulfonyl)indole
• CAS NO: 228412-76-8
• Molecular Weight: 316.337
• Mol File: 228412-76-8.mol

Chemical Properties

• CAS DataBase Reference: 3-nitro-1-(p-toluenesulfonyl)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-nitro-1-(p-toluenesulfonyl)indole(228412-76-8)
• EPA Substance Registry System: 3-nitro-1-(p-toluenesulfonyl)indole(228412-76-8)

Safety Data

• Hazardous Substances Data: 228412-76-8(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 4770-03-0 3-nitro-1H-indole 
• 31271-90-6 1-(p-toluenesulfonyl)-1H-indole 

Relevant articles and documents

Enantioselective formal [4+2] cycloadditions to 3-nitroindoles by trienamine catalysis: Synthesis of chiral dihydrocarbazoles

The first enantioselective formal [4+2] cycloadditions of 3-nitroindoles are presented. By using 3-nitroindoles in combination with an organocatalyst, chiral dihydrocarbazole scaffolds are formed in moderate to good yields (up to 87 %) and enantioselectivities (up to 97 % ee). The reaction was extended to include enantioselective [4+2] cycloadditions of 3-nitrobenzothiophene. The reaction proceeds through a [4+2] cycloaddition/elimination cascade under mild reaction conditions. Furthermore, a diastereoselective reduction of an enantioenriched cycloadduct is presented. The mechanism of the reaction is discussed based on experimental and computational studies. A formal event: Enantioselective formal [4+2] cycloadditions of 3-nitroindoles in the presence of an organocatalyst are presented. Chiral dihydrocarbazole scaffolds are formed in moderate to good yields. The reaction also proceeds with 3-nitrobenzothiophene. The mechanism of the reaction is discussed based on experimental and computational studies.

Dearomatization of 3-Nitroindoles with Highly γ-Functionalized Allenoates in Formal (3+2) Cycloadditions

3-Nitroindoles are easily reacted with highly substituted γ-allenoates in the presence of a commercially available phosphine catalyst. For instance, allenoates derived from biomolecules such as amino and deoxycholic acids are combined for the first time w

Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates

The efficient phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles with allenoates has been successfully developed, providing a facile access to cyclopenta[b]indolines with good to excellent yields and high diastereoselectivities. This strategy features mild reaction conditions, high functional group tolerance, and scalability. Additionally, the 2-nitrobenzofuran and 2-nitrobenzothiophene were good dearomative [3+2] annulation partners.

Stereodivergent Synthesis of Tetrahydrofuroindoles through Pd-Catalyzed Asymmetric Dearomative Formal [3+2] Cycloaddition

A stereodivergent synthesis of tetrahydrofuroindoles through palladium-catalyzed asymmetric dearomative formal [3+2] cycloaddition of nitroindoles with epoxybutenes was developed. The polarity of the solvent was found to play a key role in the diastereoselectivity. In toluene, good to excellent yields (70–99 %), diastereoselectivity (87/13->95/5 d.r.), and enantioselectivity (85/15–94/6 e.r.) were obtained, regardless of the properties of the substituents on nitroindoles. In acetonitrile, tetrahydrofuroindoles of a different diastereoisomer were produced with good to excellent yields (75–98 %) and stereoselectivity (78/22–93/7 d.r., 93/7–99/1 e.r.). Mechanistic studies were conducted to illustrate the origin of the diastereodivergency. The kinetic experiments indicate that the rate-determining step of this reaction is different in different solvents. ESI-MS experiments also support the existence of key palladium complex intermediates and the catalytic cycle of the reaction.

Palladium(0)-Catalyzed Dearomative [3 + 2] Cycloaddition of 3-Nitroindoles with Vinylcyclopropanes: An Entry to Stereodefined 2,3-Fused Cyclopentannulated Indoline Derivatives

The palladium(0)-catalyzed diastereoselective dearomative cyclopentannulation of 3-nitroindoles with vinylcyclopropanes is described. This straightforward and highly atom-economical method leads to a wide range of functionalized indolines in good yields a

Catalytic C-2 Allylation of Indoles by Electronic Modulation of the Indole Ring and its Application to the Synthesis of Functionalized Carbazoles

We report a palladium-catalyzed C-2 allylation of indoles and subsequent cyclization of the allylated indoles. The electronic effects of chloro and ester groups that can be readily installed at the C-3 position of indoles facilitated a highly efficient C–H allylation at the C-2 position. The resulting 2-allyl-3-chloroindoles were found to be suitable substrates for benzannulation reactions with alkynes and norbornadiene as an acetylene synthon. This approach, utilizing readily available indoles, allyl acetates, and norbornadiene, allows a rapid access to complex carbazoles. (Figure presented.).

Diels-Alder reactions of N-tosyl-3-nitroindole and dienamides: Synthesis of intermediates of Aspidospermine alkaloids

N-tosyl-3-nitroindole undergoes high yielding Diels-Alder reactions with 1-(N-acyl-N-alkylamino)-1,3-butadienes in a regioselective manner, to afford advanced intermediates for the synthesis of Aspidospermine alkaloids.